ChemInform Abstract: Synthesis and Antimicrobial Evaluation of Some Alkoxyphthalimide Derivatives of Naphthyridine.

Bhambi, Dinesh; Salvi, Vijay Kumar; Bapna, Archita; Pemawat, Gangotri; Talesara, G. L.

doi:10.1002/chin.200938146

Cited by 5 publications

(4 citation statements)

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“…Compounds having phthalimide scaffold exhibit anti-inflammatory [ 8 ], anticancer [ 9 ], antibacterial [ 10 ], HIV-1 RT [ 11 , 12 ], and HIV-1 integrase inhibitory [ 13 ] activities. An extensive perusal of literature revealed that little work has been done on phthalimides and tetrahydrophthalimide as NNRTIs.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase

2013

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BackgroundNon-nucleoside reverse transcriptase inhibitors (NNRTIs) are one of the key components in highly active anti-retroviral therapy because of their high specificity and less toxicity. NNRTIs inhibit reverse transcriptase enzyme by binding to the allosteric site, which is 10Å away from the active site. Rapid emergence of resistance is the major problem with all anti-HIV agents. Hence, there is continuous need to develop novel anti-HIV agents active against both drug sensitive and resistance strains.ResultsAll the 16 synthesized 2-(1,3-dioxo-3a,4-dihydro-1H-isoindol-2(3H,7H,7aH)-yl)-N-(substitutedphenyl) acetamide 4(a-p) analogs were characterized by Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, mass spectroscopy, and elemental analysis. Lipinski rule of five parameters and molecular parameters like solubility, drug likeness, and drug score were derived for designed analogs using online servers like Molinspiration and Osiris property explorer. Synthesized compounds were evaluated for their HIV-1 reverse transcriptase inhibitor activity by HIV-1 RNA-dependent DNA polymerase activity assay at 2 and 20 μM concentrations.ConclusionsAmong the 16 synthesized compounds, 4a, 4b, 4f, 4g, 4k, and 4l showed weak reverse transcriptase inhibitor activity at 20 μM concentration. For the designed compounds, there was no correlation observed between molecular modeling and in vitro studies.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase

2013

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“…Furthermore, many literatures have investigated the phthalimide derivatives due to their diverse range of biological activities such as antimicrobial [2][3][4][5], antiviral [6,7], anticancer [8,9], anti-inflammatory [10,11],antiepileptic [12,13], antihyperlipidimic [14,15], antihyperglycemic [16], anxiolytic [17], etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Evaluation of Newly Synthesized Compounds With Phthalimide Skeleton

2017

Egypt. J. Chem.

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“…Some of them are used for treatment of different diseases such as infectious diseases, 1) tuberculosis, 2) AIDS, 3) tumors, 4) multiple myeloma, 5) inflammatory diseases, 6) asthma, 7) diabetes, 8) hyperlipidemia, 9) convulsion, 10) depression. 11) Recently, they are evaluated as anti-Alzheimer's agents.…”

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Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment

Hemdan

El‐Sayed

2016

Chem. Pharm. Bull.

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Phthalimidoacetyl isothiocyanate underwent addition-cyclization reactions with some nitrogen and carbon nucleophilic reagents. Simultaneous or subsequent cyclization of the obtained adducts gave target heterocyclic systems such as 1,2,4-triazoles, 1,3-diazines, 1,3-oxazines and thiourea attached to a phthalimido moiety. The antimicrobial activity of the synthesized compounds was tested.Key words phthalimidoacetyl isothiocyanate; 1,2,4-triazol; 1,3-diazine; 1,3-oxazine; thiourea; antimicrobial are well known.In the past few years the authors have been involved in the uses of aroyl isothiocyanates [17][18][19][20] and acyl isothiocyanates [21][22][23][24] in different synthetic strategies of target heterocycles. Studies on the chemistry of aroyl and/or acyl isothiocyanates have established the value of these compounds as starting materials in the synthesis of a wide variety of heterocyclic systems and thiourea derivatives. [17][18][19][20][21][22][23][24][25][26][27] Based on the previous work, we have been synthesized variety of heterocyclic systems bearing phthalimido moiety by using 2-phthalimidobenzoyl isothiocyanate 19) and phthalimidoacyl isothiocyanate.22) In the current study, a further stage reactions of phthalimidoacetyl isothiocyanate was performed. Results and DiscussionTreatment of a solution of phthalimidoacetyl isothiocyanate 1 in a dry acetonitrile with 2-cyanoacetohydrazide at room temperature gave thiosemicarbazide derivative 2 in a good yield. On the other hand, the reaction of a mixture of isothiocyanate 1 and 2-cyanoacetohydrazide in acetonitrile under refluxing conditions produced 1,2,4-triazole derivative 3 in one pot-reaction. However, boiling a solution of the adduct 2 in acetonitrile also gave the 1,2,4-triazole derivative 3. Refluxing of compound 3 in ethanolic-hydrochloric acid mixture afforded ester derivative 4. On the other hand, when a solution of 3 in ethanol was boiled with a catalytic amount of sodium hydroxide, followed by acidification with dilute HCl furnished a carboxylic acid derivative 6 as illustrated in Chart 1.The structures of the synthesized compounds 2-4 and 6 were elucidated from their microanalytical and spectral data. Thus, their IR spectra displayed bands corresponding to NH, CO and C=S, as well as stretching band of CN group for compounds 2 and 3. The 1 H-NMR spectra of the synthesized compounds are in accord with their proposed structures as they showed signals for aromatic protons and aliphatic protons in addition to NH protons in the downfield region exchangeable with D 2 O. The appearance of an exchangeable broad singlet signal for compound 4, at δ: 7.16 ppm corresponds to SH proton suggests its existence entirely as aromatic triazole structure. The relatively high δ value of SH proton suggests chelation shown (Chart 1). The 1 H-NMR spectrum of compound 6 showed the absence of a signal corresponding to CH 2 protons in the up field region, instead it revealed two olefinic signals at δ: 5.88 and 5.94 ppm integrated to one proton. These observations suggest that...

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ChemInform Abstract: Synthesis and Antimicrobial Evaluation of Some Alkoxyphthalimide Derivatives of Naphthyridine.

Cited by 5 publications

References 0 publications

Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase

Design and synthesis of tetrahydrophthalimide derivatives as inhibitors of HIV-1 reverse transcriptase

Synthesis, Characterization and Antimicrobial Evaluation of Newly Synthesized Compounds With Phthalimide Skeleton

Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment

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